Nikki Glaser and her boyfriend Chris Convy have been in an on-again, off-again relationship for over a decade. Glaser admitted that her fear of committing to something forever has contributed to their multiple breakups. She mentioned that they have separated about five times in 10 years, with one break lasting three years. Glaser confessed to initially misrepresenting herself in the beginning of their relationship, wanting to be agreeable and avoid conflicts to keep the relationship intact.
The couple met in 2013 on the set of Glaser’s MTV show, Nikki & Sara Live, where Convy was a producer. Glaser, who had recently quit drinking, was initially put off by Convy’s outgoing personality and assumed he was a heavy drinker. However, when she found out he was also sober, she developed a crush on him. Glaser reminisced about how she pined for him from afar like in Jim and Pam from The Office, sharing that he was her first real boyfriend and she had her first boyfriend at the age of 24.
In 2016, Convy continued to work with Glaser, producing her show Not Safe With Nikki Glaser on Comedy Central. Unfortunately, the show was canceled after one season, coinciding with their breakup. In 2020, amidst the pandemic, Glaser moved back to St. Louis and sold her docuseries Welcome Home Nikki Glaser to E! network. She revealed that she began seeing Convy again off camera, wanting to date someone who would also appear on her show. Convy agreed to be on camera with her, highlighting how much he loved her and wanting to share their relationship publicly.
In 2022, Glaser and Convy briefly split in September, prompting a reevaluation of their goals and priorities. Glaser expressed that they had both originally agreed on not wanting marriage or kids, but with Convy in his 40s and Glaser in her late 30s, their perspectives had shifted. They discussed the direction of their relationship and where it was leading. By 2024, Glaser opened up further about their relationship on SiriusXM’s The Howard Stern Show, revealing that they had broken up in the past over her podcast confessions. Convy expressed feeling like he didn’t recognize the person Glaser was discussing on her podcast and urged her to stop lying. Glaser admitted that she still struggled with abandonment issues and fears Convy being mad at her, but acknowledged she had improved in not lying as much.
Throughout their relationship, Glaser and Convy have faced challenges and periods of separation but have also shown growth and communication in working through those issues. Glaser’s fear of commitment and past tendencies to lie have been areas of struggle, but with Convy’s support, she has learned to be more honest and true to herself. The couple’s journey has included moments of reconciliation, understanding, and reevaluation, as they navigate their changing priorities and goals together. Their story showcases the complexities of long-term relationships and the importance of honest communication in overcoming obstacles.
